What I’d start with
One monthly checklist format and a small agreed group of clients.

BOOKKEEPERS
For a bookkeeper or small practice spending too much of month-end asking clients for the same paperwork. Make the outstanding list easier to keep current.
See the automation flowIllustrative example · a possible starting point for your business
THE PROBLEM
A client has sent some receipts, the bank statement is still missing and one attachment came in on a different thread. Before you can get to the work, you have to piece together what has arrived and what to ask for again.
THE SOLUTION
I’d give each client and month a checklist, with links to its document folder. Agreed naming rules mark likely arrivals for your review, and a scheduled check prepares a request for the remaining items.
At agreed intervals, check the files in each client’s monthly folder.
Match files to named items. Mark uncertain matches for you to verify.
Prepare a client-specific email listing only the outstanding items.
Check the latest arrivals and edit or approve the request.
WHEN SOMETHING NEEDS CHECKINGA file is unclear, duplicated or for the wrong month?
Leave the item unresolved and show you the file to check. A filename alone never proves the paperwork is complete.
WHAT YOU GET
Get the remaining questions in one place, with a current status and links to the files you need to verify.
Illustrative checklist. The checklist tracks arrivals; you check whether each document is complete and usable.
INTEGRATIONS & HOSTING
| Tool | Its part in the workflow |
|---|---|
| Google Drive | Holds each client’s monthly folder, with access separated by client. |
| Google Sheets | Tracks expected documents, received files and items you have verified. |
| Gmail | Holds one draft request per client and month, ready for review. |
For a Google Workspace practice, I’d use Google Apps Script to connect Drive, Sheets and Gmail using scheduled checks and naming rules.
Apps Script runs on Google’s servers under an agreed business account. Client files would stay in your controlled Drive folders. I’d check usage limits, access and support arrangements before starting.
A SENSIBLE FIRST PROJECT
One monthly checklist format and a small agreed group of clients.
Compare time spent assembling each request and count repeat chasers for items already received.
Client folders stay separate. Unclear files need review, and existing drafts are updated rather than duplicated.
Tell me how it works today. If we agree a suitable first automation, I’ll build it for free and give you 30 days to try it. We agree the ongoing monthly price and any software costs before starting.